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Fluoroaziridines as novel substrates in the modified Petasis reaction: synthesis of monofluorinated propargyl amines |
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| Authors: | Alexander S Konev Mikhail S Novikov Kourosch Abbaspour Tehrani |
| Institution: | a Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Petrodvorets, Russia b Faculty of Sciences, Department of Applied Biological Sciences, Laboratory for Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium |
| Abstract: | Reaction of 2-fluoroaziridines with potassium alkynyltrifluoroborates in the presence of BF3·OEt2 leads to fluorinated propargyl amines in moderate to good yields. The reaction proceeds as an in situ isomerization of 2-fluoroaziridines to α-fluorinated imines, followed by the reaction of the imine with alkynyldifluoroborane, which is generated in situ from the potassium alkynyltrifluoroborates and BF3·OEt2. |
| Keywords: | Fluoroaziridines Fluorinated amines Fluorinated aldimines Boron Petasis |
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